Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone

doi:10.6023/cjoc201901052

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2075-2083.DOI: 10.6023/cjoc201901052 Previous Articles Next Articles

Notes

温度对氮杂环卡宾催化下α-溴代烯醛与烯胺酮的[3+3]环化反应影响

王占林, 李如一, 钱辉旻, 姚昌盛

江苏省功能材料绿色合成重点实验室江苏师范大学化学与材料科学学院徐州 221116

收稿日期:2019-01-30 修回日期:2019-03-13 发布日期:2019-03-21
通讯作者: 姚昌盛 E-mail:csyao@jsnu.edu.cn
基金资助:
国家自然科学基金（Nos.21871113，21372101）资助项目.

Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone

Wang Zhanlin, Li Ruyi, Qian Huimin, Yao Changsheng

Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116

Received:2019-01-30 Revised:2019-03-13 Published:2019-03-21
Contact: 10.6023/cjoc201901052 E-mail:csyao@jsnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21871113, 21372101).

1. Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone.PDF(1901KB)

Abstract

The regioselectivity of N-heterocyclic carbene (NHC)-catalyzed[3+3] annulation of α-bromoenal with enaminone is dependent on the temperature. The reactions performed at 35℃ could regiospecifically give the derivatives of fused pyranone instead of previously reported quinolones, which provided a new shortcut to pyranone with mild reaction condition, broad substrate scope, high yields and operational simplicity.

Key words: N-heterocyclic carbene (NHC), α-bromoenal, enaminone, [3+3]annulation

Cite this article

Wang Zhanlin, Li Ruyi, Qian Huimin, Yao Changsheng. Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone[J]. Chin. J. Org. Chem., 2019, 39(7): 2075-2083.

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温度对氮杂环卡宾催化下α-溴代烯醛与烯胺酮的[3+3]环化反应影响

Effect of Temperature on N-Heterocyclic Carbene-Catalyzed[3+3] Annulation of α-Bromoenal with Enaminone

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